- 関
- hetacillin
WordNet
- a light soft silver-white metallic element of the alkali metal group; oxidizes rapidly in air and reacts violently with water; is abundant in nature in combined forms occurring in sea water and in carnallite and kainite and sylvite (同)K, atomic number 19
PrepTutorEJDIC
- ポタシウム,カリウム(金属元素;化学記号はK)
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/06/21 12:26:55」(JST)
[Wiki en表示]
Hetacillin
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Systematic (IUPAC) name |
(2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
Clinical data |
Trade names |
Hetacin |
AHFS/Drugs.com |
Veterinary Use |
Legal status |
℞-only (US) |
Routes |
Intramammary injection |
Identifiers |
CAS number |
3511-16-8 Y |
ATC code |
J01CA18 |
PubChem |
CID 193260 |
DrugBank |
DB00739 |
ChemSpider |
167708 Y |
UNII |
TN4JSC48CV Y |
KEGG |
D01074 N |
ChEMBL |
CHEMBL1201116 N |
Chemical data |
Formula |
C19H23N3O4S |
Mol. mass |
389.469 g/mol |
SMILES
- O=C(O)[C@@H]3N4C(=O)[C@@H](N2C(=O)C(c1ccccc1)NC2(C)C)[C@H]4SC3(C)C
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InChI
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InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11?,12-,13+,16-/m1/s1 Y
Key:DXVUYOAEDJXBPY-XQERAMJGSA-N Y
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N (what is this?) (verify) |
Hetacillin is a beta-lactam antibiotic that is part of the aminopenicillin family. It is a prodrug and it has no antibacterial activity itself,[1] but quickly splits of acetone in the human body to form ampicillin,[2] which is active against a variety of bacteria.
Administration
Hetacillin can be administered orally.[2] The potassium salt, hetacillin potassium, is administered by injection, either intravenously or intramuscularly.[citation needed] It is sold under the trade name Hetacin for intramammary injection in veterinary use.[3]
Hetacillin was removed from the market for human use when the discovery was made that it is actually cleaved in the gastrointestinal tract to formaldehyde and had no advantages over ampicillin.[citation needed]
Chemistry
Hetacillin is prepared from ampicillin and acetone. In aqueous solutions it is unstable, with a half life of 15 to 30 minutes at 37 °C (99 °F) and pH 7, quickly releasing acetone again.[1][4]
As opposed to ampicillin, hetacillin is only marginally broken down by the bacterial enzyme beta-lactamase, at least in vitro.[4]
References
- ^ a b Drugbank: Hetacillin
- ^ a b Sutherland, R.; Robinson, O. P. (1967). "Laboratory and pharmacological studies in man with hetacillin and ampicillin". British medical journal 2 (5555): 804–808. PMC 1843140. PMID 5182358. edit
- ^ Hetacin-K Intramammary Infusion for Veterinary Use
- ^ a b Faine, S.; Harper, M. (1973). "Independent antibiotic actions of hetacillin and ampicillin revealed by fast methods". Antimicrobial agents and chemotherapy 3 (1): 15–18. PMC 444353. PMID 4597707. edit
Antibacterials: cell envelope antibiotics (J01C-J01D)
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Intracellular |
- inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
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Glycopeptide |
- inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
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β-lactams/
(inhibit PBP
cross-links) |
Penicillins
(penams)
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Extended sp.
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- aminopenicillins: Amoxicillin#
- Ampicillin# (Pivampicillin
- Hetacillin
- Bacampicillin
- Metampicillin
- Talampicillin)
- Epicillin
- carboxypenicillins: Carbenicillin (Carindacillin)
- Ticarcillin
- Temocillin
- ureidopenicillins: Azlocillin
- Piperacillin
- Mezlocillin
- other: Mecillinam (Pivmecillinam)
- Sulbenicillin
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Narrow sp.
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β-lactamase sensitive
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- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
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β-lactamase resistant
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- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
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Penems
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Carbapenems
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- Biapenem
- Ertapenem
- antipseudomonal (Doripenem
- Imipenem
- Meropenem)
- Panipenem
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Cephalosporins/Cephamycins
(cephems)
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1st (PEcK)
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- Cefazolin#
- Cefacetrile
- Cefadroxil
- Cefalexin
- Cefaloglycin
- Cefalonium
- Cefaloridine
- Cefalotin
- Cefapirin
- Cefatrizine
- Cefazedone
- Cefazaflur
- Cefradine
- Cefroxadine
- Ceftezole
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2nd (HEN)
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- Cefaclor
- Cefamandole
- Cefminox
- Cefonicid
- Ceforanide
- Cefotiam
- Cefprozil
- Cefbuperazone
- Cefuroxime
- Cefuzonam
- cephamycin (Cefoxitin
- Cefotetan
- Cefmetazole)
- carbacephem (Loracarbef)
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3rd
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- Cefixime#
- Ceftriaxone#
- antipseudomonal (Ceftazidime#
- Cefoperazone)
- Cefcapene
- Cefdaloxime
- Cefdinir
- Cefditoren
- Cefetamet
- Cefmenoxime
- Cefodizime
- Cefotaxime
- Cefpimizole
- Cefpiramide
- Cefpodoxime
- Cefsulodin
- Cefteram
- Ceftibuten
- Ceftiolene
- Ceftizoxime
- oxacephem (Flomoxef
- Latamoxef ‡)
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4th (antips-)
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- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
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5th
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- Ceftobiprole
- Ceftaroline fosamil
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Veterinary
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- Ceftiofur
- Cefquinome
- Cefovecin
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Monobactams
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- Aztreonam
- Tigemonam
- Carumonam
- Nocardicin A
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β-lactamase inh.
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- penam (Sulbactam
- Tazobactam)
- clavam (Clavulanic acid)
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Combinations
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- Amoxicillin/clavulanic acid#
- Imipenem/cilastatin#
- Ampicillin/flucloxacillin
- Ampicillin/sulbactam (Sultamicillin)
- Piperacillin/tazobactam
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Other |
- polymyxins/detergent (Colistin
- Polymyxin B)
- depolarizing (Daptomycin)
- hydrolyze NAM-NAG (Lysozyme)
- Gramicidin
- Isoniazid
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a (t)/gr-p (c)/gr-o
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drug (J1p, w, n, m, vacc)
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UpToDate Contents
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English Journal
- [Clinical evaluation of Versapen (hetacillin potassium)].
- Sternadel Z, Mazurek J, Sliwiński W, Peksa A, Wiacek J.
- Ginekologia polska.Ginekol Pol.1976 Feb;47(2):213-5.
- PMID 1254196
- [Clinical experiments with a new derivative of 6-aminopenicillanic acid: hetacillin potassium].
- Soranzo ML, Bosio G.
- Minerva medica.Minerva Med.1972 Nov 17;63(82):4453-8.
- PMID 4565935
Japanese Journal
- 泌尿器科領域におけるPotassium hetacillin(VERSAPEN "Bristol")の使用経験
- 泌尿器科領域におけるPotassium Hetacillin(Versapen)の使用経験 : 第87回熊本地方会
- 尿路感染症に対するPotassium Hetacillin(Versapen'Bristol')の治験
Related Links
- HETACILLIN POTASSIUM - chemical information, properties, structures, articles, patents and more chemical data. Enter your search term above and find: · CAS Numbers · Molecular Formulas · Synonyms · Sites/Web Search · Suppliers
- hetacillin [het″ah-sil´in] a semisynthetic penicillin that is converted in the body to ampicillin and has actions and uses similar to those of ampicillin. hetacillin a semisynthetic penicillin, which is converted in the body to ampicillin, and ...
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- 英
- hetacillin、hetacillin potassium
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- ヘタシリンカリウム
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- 英
- hetacillin potassium
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ヘタシリン
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- hetacillin potassium